US6068835A - Cosmetic compositions for hair treatment containing dendrimers or dendrimer conjugates - Google Patents
Cosmetic compositions for hair treatment containing dendrimers or dendrimer conjugates Download PDFInfo
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- US6068835A US6068835A US08/883,924 US88392497A US6068835A US 6068835 A US6068835 A US 6068835A US 88392497 A US88392497 A US 88392497A US 6068835 A US6068835 A US 6068835A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/731—Cellulose; Quaternized cellulose derivatives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/736—Chitin; Chitosan; Derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8105—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- A61K8/8111—Homopolymers or copolymers of aliphatic olefines, e.g. polyethylene, polyisobutene; Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
- A61K8/8176—Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
- A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/006—Antidandruff preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/04—Preparations for permanent waving or straightening the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/54—Polymers characterized by specific structures/properties
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/57—Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02D—CONTROLLING COMBUSTION ENGINES
- F02D2200/00—Input parameters for engine control
- F02D2200/02—Input parameters for engine control the parameters being related to the engine
- F02D2200/06—Fuel or fuel supply system parameters
- F02D2200/0606—Fuel temperature
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/01—Aerosol hair preparation
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/16—Dendrimers and dendritic polymers
Definitions
- the present invention relates to a cosmetic composition for hair treatment with a content of at least one dendrimer or dendrimer conjugate.
- hair styling plays a special roll in providing that pleasing outer appearance.
- Well cared for hair is the basis for a pleasing hair style.
- An entire series of hair treatment compositions such as shampoos, hair care preparations, rinses, sprayed liquid, which are applied in the widest variety of types of applications, e.g. as leave on- or rinse off-products, exists for the care and cleaning of the hair.
- three additional product categories are used for modifying the hair, namely permanent or temporary hair dye compositions, permanent hair shaping compositions in the form of mildly alkaline or acidic permanent wave and hair curling compositions and compositions that allow only a temporary shaping and stabilizing of the hair-do and are generally known as styling compositions.
- These products include hair sprays, hair lacquers, fixing lotions, fixing foams, hair gels, luster-providing products, hair creams, etc. All these agents or compositions usually contain a plurality of individual ingredients or components that fulfill a wide variety of purposes in the concerned recipe.
- one such new class of substances are the starburst dendrimers described in the following disclosure. Dendrimers are useful in all types of hair treatment compositions.
- the low molecular weight dendrimers cause a definite reduction in wet combing force and provide a good feel in acid media.
- the dry hair treated in this way has good volume and elasticity.
- the subject matter of the invention is thus a cosmetic composition for hair treatment with a content of at least one dendrimer or dendrimer conjugate in a suitable cosmetic foundation or base.
- Dendrimers are three-dimensional, highly branched oligomers and polymers with a well defined chemical structure. Generally dendrimers comprise a core made from a plurality of branches, the so-called generations, and end groups.
- Dendrimers are described in a number of patent applications. Thus building blocks made from dendrimers are described in U.S. Pat. No. 5,210,309. U.S. Pat. No. 4,102,827 and U.S. Pat. No. 4,036,808 describe making highly cationic polyelectrolytes in the form of branched polyelectrolytes or star-shaped polyelectrolytes and the use of such cationic electrolytes in conductive hydrogels. WO 93/21144 describes the production of cascade polymers. A series of applications describe the making of dendrimers and applications for pharmaceutical purposes. In EP 0 271 180 star-shaped conjugates for pharmaceutical and agricultural purposes are described.
- Dendrimers can be made in very different ways. They can be made according to the methods described in WO 93/21144 or EP 0 271 180. Additional manufacturing processes are described in U.S. Pat. No. 4,587,329, U.S. Pat. No. 4,558,120 and WO 92/14543. Furthermore a series of additional disclosures exist in which the making of dendrimers is described.
- the preferred dendrimers in the cosmetic compositions according to the invention are made from a 1,4-diaminobutane core by a stepwise Michael Addition of acrylnitrile with subsequent catalytic hydrogenation of the cyano groups to amino groups, in which dendrimers with nitrile or amino end groups are obtained.
- These dendrimers are designated as poly(iminopropan-1,3-diyl)dendrimer with nitrile and/or amino end groups.
- the cosmetic composition according to the invention preferably contains from 0.01 to 75 percent by weight, especially preferably from 0.1 to 35 percent by weight, of the at least one dendrimer or dendrimer conjugate.
- the composition according to the invention can be in the form of a hair wash composition, a hair care composition, a hair fixing composition, a hair dye composition or a hair tinting composition.
- the composition can be applied as a lotion, foam, milk, gel, cream, gel foam or spray. It can be formulated as a leave-on or as a rinse-off product.
- the cosmetic composition according to the invention can furthermore contain standard conventional cosmetic additives for hair treatment compositions, for example, solvents, such as water and lower aliphatic alcohols, e.g. ethanol, propanol and isopropanol, or glycols, such as glycerol and 1,2-propylene glycol; wetting agents or emulsifiers from the classes of anionic, cationic, amphoteric or non-ionic surface active substances or surfactants, such as fatty alcohol sulfates, alkylbenzene sulfonates, alkyltrimethyl-ammonium salts, alkylbetaines, ethoxylated fatty alcohols, ethoxylated nonylphenols, fatty acid alkanol amides, ethoxylated fatty acid esters, in an amount of from 0.1 to 30 percent by weight; perfume oils in an amount of from 0.1 to 5.0 percent by weight; turbidity-inducing agents, such as, e.g
- solubilizing agents such as ethoxylated castor oil, in an amount of from about 0.1 to 1.0 percent by weight
- dye compounds such as fluorescein sodium salt, in an amount of from about 0.1 to 1.0 percent by weight
- care-giving materials such plant and herbal extracts, protein and silk hydrolyzates, cationic resins, lanolin derivatives, in an amount of from 0.1 to 5 percent by weight
- physiologically compatible silicone derivatives such as silicone oil, silicon polymers and siloxane
- light protective agents moisture containing agents, antioxidants, radical-trapping agents, anti-flaking agents, in an amount of from about 0.1 to 2 percent by weight
- physiologically compatible organic or inorganic acids such as formic acid, glyoxylic acid, lactic acid, tartaric acid, citric acid or phosphoric acid
- natural, modified natural or synthetic polymers such as shellac, cationic polymers, anionic polymers, non
- the composition according to the invention also contains from 0.01 to 40 percent by weight, especially preferably from 0.01 to 25 percent by weight of at least one anionic, cationic, amphoteric or non-ionic surfactant and from 50 to 90 percent by weight water.
- a composition of this type can be used as a hair cleansing agent.
- the composition according to the invention contains additionally at least one natural or synthetic polymer, which is selected from the group of fixing and thickening polymers.
- the polymers can be used in amounts of from 0.01 to 25 percent by weight, preferably from 0.1 to 20 percent by weight and can be present in dissolved form or as a dispersion.
- a composition of this type including the fixing polymers can be used as a hair fixing composition.
- keratin-reducing mercapto compound e.g. cysteine, cysteamine, N-acetyl-L-cysteine
- mercaptocarboxylic acids such as thioglycolic acid or thiolactic acid
- sodium or ammonium sulfite or the salt of sulfuric acid with an organic amine for example monoethanol amine and guanidine
- an organic amine for example monoethanol amine and guanidine
- thioglycolic acid monoglycolic ester or -glycerol ester is used in a concentration of about 5 to 50 percent by weight (corresponding to a content of free thioglycolic acid of from 2 to 16 percent by weight).
- composition according to the invention for permanent hair shaping also can contain a mixture of the aforementioned keratin-reducing compounds.
- the hair is rinsed with water and subsequently oxidatively after-treated ("fixed").
- the after-treatment composition is used in an amount of from about 50 to 100 g according to the amount of the hair.
- a fixing composition according to the invention with a content of dendrimers or dendrimer conjugates and any known oxidizing agent used up to now in this sort of treatment can be used for the oxidative after-treatment.
- oxidizing agents used in this type of fixing composition include sodium and potassium bromate, sodium perborate, urea peroxide and hydrogen peroxide.
- the concentration of oxidizing agent differs according to the application time (usually about 5 to 15 minutes) and the application temperature.
- the oxidizing agent is present in the aqueous fixing composition in a concentration of from about 0.5 to 10 percent by weight.
- Both the composition according to the invention for permanent shaping of hair and also the composition for fixing hair can be present in the form of an aqueous solution or emulsion and in thickened form on an aqueous basis, especially as a cream, gel or paste.
- the curlers are removed.
- the curled hair can be given an oxidative hair treatment.
- the hair is rinsed with water, put in a hair-do and finally dried.
- the above-described process for permanent shaping of hair provides a safe and uniform shaping from the hair roots to the hair tips, an outstanding wet and dry combability, a pleasant feel and an attractive look in the dry state as well as a loose, springy and uniform permanent wave, especially in the vicinity of the hair roots.
- a hair dye composition according to the invention contains also from 0.05 to 2.0 percent by weight of at least one direct-dyeing hair dye, which, for example, can be selected from the following classes of direct-dyeing hair dye compounds: aromatic nitro dye compounds, e.g., 1,4-diamino-2-nitrobenzene; azo dye compounds, for example Acid Brown 4 (C.I. 14 805); anthraquinone dye compounds, e.g. Disperse Violet 4 (C.I. 61 105); triphenylmethane dye compounds, e.g. Basic Violet 1 (C.I. 42 535), wherein these dye compounds can have an acidic, nonionic or basic character according to the type of their substituents; and/or natural hair dye compounds, such as Henna or Reng, which do not require oxidation to develop their colors.
- aromatic nitro dye compounds e.g., 1,4-diamino-2-nitrobenzene
- azo dye compounds for example Acid Brown 4 (C
- composition according to the invention can be sprayed using a propellant or dispensed with the help of a mechanical spraying apparatus or with the help of a foam producing apparatus as a foam.
- the cosmetic composition according to the invention When the cosmetic composition according to the invention is sprayed with the help of a propellant composition, it advantageously contains from 3 to 75 percent by weight of a propellant and is filled in a pressurized container.
- Lower alkanes such as n-butane, i-butane and propane or their mixtures, or also dimethyl ether and fluorinated hydrocarbons, such as F 152 (1,1-difluoroethane) or F 134 (tetrafluoroethane) and furthermore gases at the pressures which are to be used, for example, N 2 , N 2 O and CO 2 and mixtures thereof, can be used as the propellant.
- Mechanical spraying or foam producing apparatuses are those apparatuses which allow spraying or foaming of a liquid without using a propellant.
- a spray pump or an elastic container provided with a spray valve can be used as a suitable mechanical spray apparatus.
- the composition according to the invention is filled in this container under pressure, so that the elastic container is expanded.
- the composition is continuously dispensed from the container, when the spray valve is opened, because of the contraction of the elastic container.
- a suitable mechanical foam producing apparatus e.g., the top with a foam producing device described in EP-B 0 0460 154 can be used on a flexible container.
- the cosmetic composition according to the invention is used for hair care, the following method is used.
- the composition according to the invention After washing the hair from 5 to 30 g of the composition according to the invention are distributed on the hand towel dried hair, according to the amount of hair, and allowed to act on the hair for about 3 to 15 minutes. Subsequently the composition is rinsed out of the hair, the hair is combed, a hair-do is formed as needed and the hair is dried. In a preferred embodiment of the invention the composition is allowed to remain on the hair, which means that it is not rinsed out of the hair and thus saves the user some work.
- the hair treatment composition according to the invention may include a bleaching agent so that it is in the form of the hair bleaching composition.
- composition according to the invention when the composition according to the invention is an oxidation hair dye composition, it contains from about 0.01 to 5.0 percent by weight of a suitable coupler substance and from about 0.01 to 5.0 percent by weight of a suitable developer substance.
- suitable coupler substances include resorcinol, 4-chlororesorcinol, 1-naphthol, 3-aminophenol or derivatives of m-phenylene-diamines.
- suitable developer substances include, e.g., 2,5-diaminotoluene, 2,5-diaminophenylethyl alcohol, p-aminophenol or 1,4-diaminobenzene.
- a suitable oxidizing agent such as hydrogen peroxide or its addition compounds with urea, melamine, sodium borate or sodium carbonate are used in the form of a 3- to 12- percent by weight aqueous solution, however also air oxygen can be used.
- the above composition is filled in a ratio of 94:6 with a propane-butane-propellant gas mixture.
- Example 31 80% VOC Hair spray
- Example 33 80% VOC Pump Hair Spray
- the wet combability and dry combability of hair treated with four aqueous solutions A to D according to the present invention were measured and compared with the measured wet and dry combability of hair treated with five aqueous solution containing standard hair care polymers.
- each polymer solution After preliminary combing and adjustment to a residual moisture of 50%, 0.5 ml of each polymer solution is applied to one of the individual samples uniformly and placed in a foil pocket. After an acting time of 5 minutes, the combing forces for both wet combing and also dry combing were measured after drying the wet combed strand after the wet combing.
- Table I shows the principle polymer ingredient of each tested solution and its concentration in the solution as well as the pH of the solution.
- Table II below shows the wet combing force and the dry combing force of each sample.
- the average combing force of an untreated control sample of hair amounted to 0.47N.
- the compositions A to D according to the invention have clearly reduced combing force results in comparison to those of the prior art.
- German Patent Application 196 25 928.7 of Jun. 28, 1996 is incorporated here by reference.
- This German Patent Application describes the invention described hereinabove and claimed in the claims appended herein in below and provides the basis for a claim of priority for the instant invention under 35 U.S.C. 119.
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Abstract
The hair treatment compositions are in a variety of forms including permanent shaping compositions, oxidative after-treatment compositions, hair fixing compositions, hair bleaching compositions, hair cleansing compositions, hair care compositions or hair dye compositions containing direct-dyeing dye compounds and/or a combination of at least one developer and coupler and are characterized by 0.1 to 35 percent by weight of at least one dendrimer, preferably a poly(iminopropane-1,3-diyl)-dendrimer with nitrile and/or amino end groups. Methods of hair treatment based on these hair treatment compositions are described.
Description
The present invention relates to a cosmetic composition for hair treatment with a content of at least one dendrimer or dendrimer conjugate.
A pleasing outer appearance has always been viewed as very important. Hair styling plays a special roll in providing that pleasing outer appearance. Well cared for hair is the basis for a pleasing hair style. An entire series of hair treatment compositions, such as shampoos, hair care preparations, rinses, sprayed liquid, which are applied in the widest variety of types of applications, e.g. as leave on- or rinse off-products, exists for the care and cleaning of the hair. Besides these hair care products three additional product categories are used for modifying the hair, namely permanent or temporary hair dye compositions, permanent hair shaping compositions in the form of mildly alkaline or acidic permanent wave and hair curling compositions and compositions that allow only a temporary shaping and stabilizing of the hair-do and are generally known as styling compositions. These products include hair sprays, hair lacquers, fixing lotions, fixing foams, hair gels, luster-providing products, hair creams, etc. All these agents or compositions usually contain a plurality of individual ingredients or components that fulfill a wide variety of purposes in the concerned recipe.
Thus substances were sought which are compatible in the largest possible number of recipes and which can perform a variety of functions according to the formulation. Substances which can perform two or more functions in a recipe are of special interest. The requirements for hair care include, for example, that wet hair should already have a good, pleasant feel and a good combability. A pleasant feel elasticity and volume (with the exception of "Wetlook" hair-dos) are similarly expected of dry hair.
It is an object of the present invention to find a new class of substances which fulfill the above-named requirements.
According to the invention one such new class of substances are the starburst dendrimers described in the following disclosure. Dendrimers are useful in all types of hair treatment compositions.
Indeed the low molecular weight dendrimers cause a definite reduction in wet combing force and provide a good feel in acid media. The dry hair treated in this way has good volume and elasticity.
The subject matter of the invention is thus a cosmetic composition for hair treatment with a content of at least one dendrimer or dendrimer conjugate in a suitable cosmetic foundation or base.
Dendrimers are three-dimensional, highly branched oligomers and polymers with a well defined chemical structure. Generally dendrimers comprise a core made from a plurality of branches, the so-called generations, and end groups.
Dendrimers are described in a number of patent applications. Thus building blocks made from dendrimers are described in U.S. Pat. No. 5,210,309. U.S. Pat. No. 4,102,827 and U.S. Pat. No. 4,036,808 describe making highly cationic polyelectrolytes in the form of branched polyelectrolytes or star-shaped polyelectrolytes and the use of such cationic electrolytes in conductive hydrogels. WO 93/21144 describes the production of cascade polymers. A series of applications describe the making of dendrimers and applications for pharmaceutical purposes. In EP 0 271 180 star-shaped conjugates for pharmaceutical and agricultural purposes are described. In SE 468 771 the making of polyester dendrimers and their uses as coupling components in polyester, epoxy- or polyurethane resins and their use as binder components for a series of non-cosmetic applications is claimed. WO 92/14543 describes unimolecular micelles based on cascade polymers and methods of making them. In U.S. Pat. No. 4,587,329 and U.S. Pat. No. 4,558,120 a method of making star-shaped dendrimers and their application as demulsifiers in O/W emulsions is described. The use of star-shaped dendrimers for calibration and characterization of substances with an overall dimension up to 10 μm is claimed in EP 0 247 629. A series of scientific publications disclosing methods for making dendrimers exists in addition to the above-described patents. Dendrimers can be made in very different ways. They can be made according to the methods described in WO 93/21144 or EP 0 271 180. Additional manufacturing processes are described in U.S. Pat. No. 4,587,329, U.S. Pat. No. 4,558,120 and WO 92/14543. Furthermore a series of additional disclosures exist in which the making of dendrimers is described.
The preferred dendrimers in the cosmetic compositions according to the invention are made from a 1,4-diaminobutane core by a stepwise Michael Addition of acrylnitrile with subsequent catalytic hydrogenation of the cyano groups to amino groups, in which dendrimers with nitrile or amino end groups are obtained. These dendrimers are designated as poly(iminopropan-1,3-diyl)dendrimer with nitrile and/or amino end groups. Suitable dendrimers are, e.g., marketed under the tradename 4-cascade: 1,4-diaminobutane [4]: propylamine and/or x-cascade: 1,4-diaminobutane [4]: (1-azabutylidene)x-4 : propylamine by DSM/Netherlands, wherein x=4, 8, 16, 32 or 64.
The cosmetic composition according to the invention preferably contains from 0.01 to 75 percent by weight, especially preferably from 0.1 to 35 percent by weight, of the at least one dendrimer or dendrimer conjugate. The composition according to the invention can be in the form of a hair wash composition, a hair care composition, a hair fixing composition, a hair dye composition or a hair tinting composition. The composition can be applied as a lotion, foam, milk, gel, cream, gel foam or spray. It can be formulated as a leave-on or as a rinse-off product.
The cosmetic composition according to the invention can furthermore contain standard conventional cosmetic additives for hair treatment compositions, for example, solvents, such as water and lower aliphatic alcohols, e.g. ethanol, propanol and isopropanol, or glycols, such as glycerol and 1,2-propylene glycol; wetting agents or emulsifiers from the classes of anionic, cationic, amphoteric or non-ionic surface active substances or surfactants, such as fatty alcohol sulfates, alkylbenzene sulfonates, alkyltrimethyl-ammonium salts, alkylbetaines, ethoxylated fatty alcohols, ethoxylated nonylphenols, fatty acid alkanol amides, ethoxylated fatty acid esters, in an amount of from 0.1 to 30 percent by weight; perfume oils in an amount of from 0.1 to 5.0 percent by weight; turbidity-inducing agents, such as, e.g., ethylene glycol distearates, in an amount of from about 0.2 to 5.0 percent by weight; pearlescence agents, such as a mixture of fatty acid monoalkylol amides and ethylene glycol distearate, in an amount of from about 1.0 to 10 percent by weight; bactericidal and fungicidal materials, such as 2,4,4-trichloro-2-hydroxydiphenyl ether or methyl chloroisothiazoline, in an amount of from 0.01 to 1.0 percent by weight; thickeners, such as coconut oil fatty acid diethanol amide in an amount of about 0.2 to 3.0 percent by weight; buffer substances, e.g. sodium citrate or sodium phosphate, in an amount of 0.1 to 1.0 percent by weight; solubilizing agents, such as ethoxylated castor oil, in an amount of from about 0.1 to 1.0 percent by weight; dye compounds, such as fluorescein sodium salt, in an amount of from about 0.1 to 1.0 percent by weight; care-giving materials, such plant and herbal extracts, protein and silk hydrolyzates, cationic resins, lanolin derivatives, in an amount of from 0.1 to 5 percent by weight; physiologically compatible silicone derivatives, such as silicone oil, silicon polymers and siloxane; light protective agents, moisture containing agents, antioxidants, radical-trapping agents, anti-flaking agents, in an amount of from about 0.1 to 2 percent by weight; physiologically compatible organic or inorganic acids, such as formic acid, glyoxylic acid, lactic acid, tartaric acid, citric acid or phosphoric acid; natural, modified natural or synthetic polymers, such as shellac, cationic polymers, anionic polymers, non-ionic polymers, amphoteric polymers, chitosan, chitin or chitosan derivatives; direct-dyeing hair dye compounds, which are developed by oxidation, oxidizing agents, reducing agents, fatty alcohols, sheen-giving agents, vitamins, softeners, combability improving agents, defattying agents, defoaming agents and propellant gases, such as fluorinated hydrocarbons, dimethylether, hydrocarbons and compressed gases.
In a preferred embodiment of the invention the composition according to the invention also contains from 0.01 to 40 percent by weight, especially preferably from 0.01 to 25 percent by weight of at least one anionic, cationic, amphoteric or non-ionic surfactant and from 50 to 90 percent by weight water. A composition of this type can be used as a hair cleansing agent.
In a further preferred embodiment the composition according to the invention contains additionally at least one natural or synthetic polymer, which is selected from the group of fixing and thickening polymers. The polymers can be used in amounts of from 0.01 to 25 percent by weight, preferably from 0.1 to 20 percent by weight and can be present in dissolved form or as a dispersion. A composition of this type including the fixing polymers can be used as a hair fixing composition.
When the composition according to the invention is a permanent shaping composition, it contains from 0.5 to 15 percent by weight of at least one keratin-reducing mercapto compound and is present advantageously as an aqueous, alkaline or weakly acidic (pH=5 to 10) preparation, which contains as keratin-reducing mercapto compound, e.g. cysteine, cysteamine, N-acetyl-L-cysteine, mercaptocarboxylic acids, such as thioglycolic acid or thiolactic acid, or salts of mercaptocarboxylic acids, such as ammonium and guanidine salts of thioglycolic acid or thiolactic acid.
The required alkalinity is adjusted by addition of ammonia, organic amines, ammonium and alkali carbonates or alkali hydrogen carbonates. However the composition according to the invention can also be a neutral or acidic hair shaping composition (pH=4.5 to 7) which has an effective content of sulfites or mercaptocarboxylic acid esters.
In the first case advantageously sodium or ammonium sulfite or the salt of sulfuric acid with an organic amine, for example monoethanol amine and guanidine, is used in a concentration of about 2 to 12 percent by weight (calculated as SO2). In the later case thioglycolic acid monoglycolic ester or -glycerol ester is used in a concentration of about 5 to 50 percent by weight (corresponding to a content of free thioglycolic acid of from 2 to 16 percent by weight).
The composition according to the invention for permanent hair shaping also can contain a mixture of the aforementioned keratin-reducing compounds.
After a sufficient acting time for permanent shaping of hair, which amounts to from about 10 to 30 minutes, according to the condition of the hair, the pH and the shaping effectiveness of the hair shaping agent as well as the application temperature, the hair is rinsed with water and subsequently oxidatively after-treated ("fixed"). The after-treatment composition, is used in an amount of from about 50 to 100 g according to the amount of the hair.
A fixing composition according to the invention with a content of dendrimers or dendrimer conjugates and any known oxidizing agent used up to now in this sort of treatment can be used for the oxidative after-treatment. For example, oxidizing agents used in this type of fixing composition include sodium and potassium bromate, sodium perborate, urea peroxide and hydrogen peroxide.
The concentration of oxidizing agent differs according to the application time (usually about 5 to 15 minutes) and the application temperature. Usually the oxidizing agent is present in the aqueous fixing composition in a concentration of from about 0.5 to 10 percent by weight.
Both the composition according to the invention for permanent shaping of hair and also the composition for fixing hair can be present in the form of an aqueous solution or emulsion and in thickened form on an aqueous basis, especially as a cream, gel or paste.
Subsequently the curlers are removed. In cases where it is required, the curled hair can be given an oxidative hair treatment. Then the hair is rinsed with water, put in a hair-do and finally dried.
The above-described process for permanent shaping of hair provides a safe and uniform shaping from the hair roots to the hair tips, an outstanding wet and dry combability, a pleasant feel and an attractive look in the dry state as well as a loose, springy and uniform permanent wave, especially in the vicinity of the hair roots.
A hair dye composition according to the invention contains also from 0.05 to 2.0 percent by weight of at least one direct-dyeing hair dye, which, for example, can be selected from the following classes of direct-dyeing hair dye compounds: aromatic nitro dye compounds, e.g., 1,4-diamino-2-nitrobenzene; azo dye compounds, for example Acid Brown 4 (C.I. 14 805); anthraquinone dye compounds, e.g. Disperse Violet 4 (C.I. 61 105); triphenylmethane dye compounds, e.g. Basic Violet 1 (C.I. 42 535), wherein these dye compounds can have an acidic, nonionic or basic character according to the type of their substituents; and/or natural hair dye compounds, such as Henna or Reng, which do not require oxidation to develop their colors.
The composition according to the invention can be sprayed using a propellant or dispensed with the help of a mechanical spraying apparatus or with the help of a foam producing apparatus as a foam.
When the cosmetic composition according to the invention is sprayed with the help of a propellant composition, it advantageously contains from 3 to 75 percent by weight of a propellant and is filled in a pressurized container.
Lower alkanes, such as n-butane, i-butane and propane or their mixtures, or also dimethyl ether and fluorinated hydrocarbons, such as F 152 (1,1-difluoroethane) or F 134 (tetrafluoroethane) and furthermore gases at the pressures which are to be used, for example, N2, N2 O and CO2 and mixtures thereof, can be used as the propellant.
Mechanical spraying or foam producing apparatuses are those apparatuses which allow spraying or foaming of a liquid without using a propellant. For example, a spray pump or an elastic container provided with a spray valve can be used as a suitable mechanical spray apparatus. The composition according to the invention is filled in this container under pressure, so that the elastic container is expanded. The composition is continuously dispensed from the container, when the spray valve is opened, because of the contraction of the elastic container. As a suitable mechanical foam producing apparatus, e.g., the top with a foam producing device described in EP-B 0 0460 154 can be used on a flexible container.
When the cosmetic composition according to the invention is used for hair care, the following method is used.
After washing the hair from 5 to 30 g of the composition according to the invention are distributed on the hand towel dried hair, according to the amount of hair, and allowed to act on the hair for about 3 to 15 minutes. Subsequently the composition is rinsed out of the hair, the hair is combed, a hair-do is formed as needed and the hair is dried. In a preferred embodiment of the invention the composition is allowed to remain on the hair, which means that it is not rinsed out of the hair and thus saves the user some work.
The hair treatment composition according to the invention may include a bleaching agent so that it is in the form of the hair bleaching composition.
When the composition according to the invention is an oxidation hair dye composition, it contains from about 0.01 to 5.0 percent by weight of a suitable coupler substance and from about 0.01 to 5.0 percent by weight of a suitable developer substance. For example, suitable coupler substances include resorcinol, 4-chlororesorcinol, 1-naphthol, 3-aminophenol or derivatives of m-phenylene-diamines. Suitable developer substances include, e.g., 2,5-diaminotoluene, 2,5-diaminophenylethyl alcohol, p-aminophenol or 1,4-diaminobenzene. For development of the hair color a suitable oxidizing agent such as hydrogen peroxide or its addition compounds with urea, melamine, sodium borate or sodium carbonate are used in the form of a 3- to 12- percent by weight aqueous solution, however also air oxygen can be used.
The following examples should illustrate the subject matter of the present invention, but without limiting the appended claims provided hereinbelow.
Example 1: Permanent Wave Shaping Composition
______________________________________
A B
______________________________________
7.4 g -- 4-cascade: 1,4-diaminobutane[4]:
propylamine
-- 10.0 g 32-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.28 : propylamine
8.0 g 8.0 g thioglycolic acid
2.6 g 2.6 g ammonium hydrogen carbonate
0.3 g 0.3 g glycerin polyethyleneglycol-(35)-
ricinate
0.3 g 0.3 g perfume
0.1 g 0.1 g octylphenol, ethoxylated with 20
Mol ethylene oxide
81.3 g 78.7 g water
100.0 g 100.0 g
8.1 8.1 pH value
______________________________________
Example 2: Permanent Wave Shaping Composition
______________________________________
7.36 g 8-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.4 : propylamine
7.06 g thiolactic acid
2.50 g L-cysteine
1.50 g Polypropylene(1)-polyethylene-
(9)-lauryl glycol ether
0.75 g perfume
0.23 g dimethyldiallylammonium chloride
80.60 g water
100.0 g
8.4 pH value
______________________________________
Example 3: Acidic Permanent Wave Shaping Composition
______________________________________
0.55 g 16-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.12 : propylamine
7.28 g monothioglycolic acid glyceryl ester
0.71 g DL-2-pyrrolidone-5-carboxylic acid
0.60 g perfume
0.50 g glycerin polyethyleneglycol-(35)-
ricinate
0.40 g octylphenol, ethoxylated with 20
Mol ethylene oxide
0.30 g vinylpyrrolidone/methacrylamidopropyl-
trimethylammonium chloride copolymer
0.20 g vinylpyrrolidone/polystyrene copolymer
89.46 g water
100.0 g
6.5 pH value
______________________________________
Example 4: Permanent Wave-Fixing Composition
______________________________________
0.5 g 8-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.4 : propylamine
10.0 g sodium bromate
3.2 g disodium hydrogen phosphate dodecahydrate
0.8 g ortho-phosphoric acid (85%)
0.5 g monosodium phosphate
85.0 g water
100.0 g
6.4 pH value
______________________________________
Example 5: Foam Fixing Composition
______________________________________
1.15 g 4-cascade: 1,4-diaminobutane[4]:
propylamine
14.00 g hydrogen peroxide (35 percent)
3.41 g o-phosphoric acid (85 percent)
1.25 g DL-2-pyrrolidone-5-carboxylic acid
0.66 g laurylaminodimethylacetobetaine
0.50 g Polypropylene-(1)-polyethylene-
(9)-lauryl glycol ether
0.20 g perfume
0.05 g p-acetainophenol
78.78 g water
100.0 g
2.2 pH value
______________________________________
Example 6: Fixing Composition
______________________________________
1.02 g 32-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.28 : propylamine
20.00 g hydrogen peroxide
3.05 g o-phosphoric acid (85 percent)
1.50 g disodiumhydrogen phosphate
1.13 g cetyltrimethylammonium chloride
0.45 g hydrogenated rhizonic oil, ethoxylated with
45 Mol ethylene oxide
0.35 g DL-2-pyrrolidone-5-carboxylic acid
0.30 g perfume
0.05 g 1-hydroxyethylidene-1,1-diphosphoric acid
72.15 g water
100.0 g
2.2 pH value
______________________________________
Example 7: Shampoo
______________________________________
0.60 g 16-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.12 : propylamine
15.90 g decylpolyglucose
3.00 g coconut oil fatty acid amidopropylbetaine
2.45 g polyethyleneglycol-(120)-methyl-
glucose dioleate
0.95 g citric acid
0.50 g perfume
0.35 g sodium benzoate
0.06 g sodium formiate
76.19 g water
100.0 g
5.6 pH value
______________________________________
Example 8: Shampoo
______________________________________
0.30 g 4-cascade: 1,4-diaminobutane[4]:
propylamine
11.62 g lauryl ether sulfate
3.00 g sodium chloride
0.37 g citric acid
0.20 g perfume
0.06 g 1,2-dibromo-2,4-dicyanobutane
87.45 g water
100.0 g
5.3 pH value
______________________________________
Example 9: Conditioning Shampoo
______________________________________
0.80 g 32-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.28 : propylamine
12.00 g laurylaminodimethylacetobetaine
6.40 g potassiumcocoyl-collagen hydrolyzate
3.50 g coconut oil fatty acid monoethanol amide
1.30 g DL-2-pyrrolidone-5-carboxylic acid
0.88 g collagen hydrolyzate
0.30 g perfume
0.23 g citric acid
0.15 g 1,2-dibromo-2,4-dicyanobutane
74.44 g water
100.0 g
5.4 pH value
______________________________________
Example 10: Defatting Shampoo
______________________________________
0.50 g 4-cascade: 1,4-diaminobutane[4]:
propylamine
11.20 g lauryl ether sulfate
5.00 g Plant Extract Extrapon Ivy of
Drago, Germany
3.00 g Plant Extract Extrapon Vanilla Special of
Drago, Germany
3.00 g coconut oil fatty acid amidopropylbetaine
2.00 g sodium chloride
1.70 g 1,2-propylene glycol
1.10 g DL-2-pyrrolidone-5-carboxylic acid
0.30 g p-hydroxybenzoic acid methyl ester
0.15 g perfume
72.05 g water
100.0 g
5.3 pH value
______________________________________
Example 11: Anti-flaking Shampoo
______________________________________
0.65 g 64-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.60 : propylamine
25.00 g monocarboxymethyl-coconutimidazoline
6.00 g 3-[(3-cocoamidopropyl)dimethylammonio]-
2-hydroxypropane sulfonate
3.00 g glyceryl stearate
1.75 g polyethyleneglycol-(120)-methylglucose
dioleate
1.20 g formic acid
1.00 g 1,2-propylene glycol
0.40 g cationic hydroxyethyl cellulose
0.40 g 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-
2(1H)-pyridone monoethanolamine salt
0.30 g perfume
0.15 g ethylenediaminetetracetic acid, sodium salt
60.15 g water
100.0 g
4.9 pH value
______________________________________
Example 12: Two-in-One Shampoo
______________________________________
0.71 g 8-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.4 : propylamine
16.52
g lauryldimethylcaroxymethylammoniumbetaine
5.00 g dioxyethylenelauryl ether
4.00 g Rewoderm ® 66 E 10 Surfactant of Rewo, Germany
2.20 g lauric acid diethanolamide
2.00 g diquaternary polydimethylsiloxane (Abil ® Quat
3272 of Goldschmidt, Germany)
0.71 g formic acid
0.40 g perfume
0.15 g 1,2-dibromo-2,4-dicyanobutane
68.31
g water
100.0
g
5.2 pH value
______________________________________
Example 13: Hair Care Composition
______________________________________
0.93 g 32-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.28 : propylamine
5.00 g glycerol monodistearate
4.00 g stearyl alcohol
2.07 g citric acid
1.13 g cetyltrimethylammonium chloride
0.50 g glycerol (86 percent)
0.50 g Plant Extract Extrapon Bambus ® of
Drago, Germany
0.30 g perfume oil
85.57 g water
100.00 g
3.4 pH value
______________________________________
Example 14: Intense Hair Care Composition
______________________________________
0.60 g 64-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.60 :propylamine
6.00 g cetylstearyl alcohol
2.00 g wool fat
1.50 g DL-2-pyrrolidone-5-carboxylic acid
1.00 g cetyltrimethylammonium chloride
0.83 g distearyldimethylammonium chloride
0.60 g 1,2-propylene glycol
0.20 g perfume
0.18 g collagen hydrolyzate
87.09 g water
100.00 g
3.2 pH value
______________________________________
Example 15: Hair Balm
______________________________________
0.50 g 16-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.12 : propylamine
6.00 g glycerylstearate/polyethyleneglycol-
(20)-cetearyl ether
4.00 g diquaternary polydimethylsiloxane (Abil ® Quat
3272 of Goldschmidt, Germany)
2.00 g cetyl alcohol
1.36 g citric acid
0.14 g 1,2-dibromo-2,4-dicyanobutane
0.12 g perfume
85.88 g water
100.00 g
3.5 pH value
______________________________________
Example 16: Hair Rinse
______________________________________
0.75 g 8-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.4 : propylamine
4.00 g cetylstearyl alcohol
1.36 g DL-2-pyrrolidone-5-carboxylic acid
0.75 g cetyltrimethylammonium chloride
0.50 g perfume
0.20 g Plant Extract Extrapon ® 5 Special of
Drago, Germany
92.44 g water
100.00 g
4.7 pH value
______________________________________
Example 17: Rinsible Hair Care Composition
______________________________________
0.40 g 32-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.28 : propylamine
2.00 g dimethyldiallylammonium chloride
1.25 g polyethyleneglyucol-(40)-sorbitan-
monopalmitate
1.00 g DL-2-pyrrolidone-5-carboxylic acid
0.10 g perfume
0.03 g cetyltrimethylammonium chloride
15.00 g ethanol
80.22 g water
100.00 g
4.2 pH value
______________________________________
Example 18: Foam-like Hair Care Composition
______________________________________
0.80 g 4-cascade: 1,4-diaminobutane[4]:
propylamine
2.00 g cationic emulsion of amine functionalized
polydimethylsiloxane (929 cationic emulsion
of DOW-Corning, Europe/Belgium)
1.30 g citric acid
0.50 g hydroxypropylcellulose (M = 1,150,000 g/mol)
0.30 g silicone wax (2501 Cosmetic Wax of Dow-
Corning, Europe/Belgium)
0.20 g perfume
0.25 g cetyltrimethylammonium chloride
0.15 g D-panthenol
0.10 g elastin hydroyzate
5.00 g propane/butane (5.0 bar)
10.00 g ethanol
79.40 g water
100.00 g
5.2 pH value
______________________________________
Example 19: Hair Fixing Composition
______________________________________
0.40 g 32-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.28 : propylamine
3.00 g vinylpyrrolidone/vinyl acetate copolymer
0.90 g formic acid
0.20 g 1,2-propylene glycol
0.15 g perfume
0.03 g cetyltrimethylammonium chloride
20.00 g water
75.22 g ethanol
100.00 g
4.7 pH value
______________________________________
Example 20: UV-Protective Lotion
______________________________________
0.60 g 16-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.12 : propylamine
2.15 g DL-2-pyrrolidone-5-carboxylic acid
1.50 g vinylpyrrolidone/vinylacetate copolymer
1.25 g vinylpyrrolidone/dimethylaminoethyl-
methacrylate copolymer
0.20 g perfume
0.15 g glycerol (85 percent)
0.10 g 2-hydroxy-4-methoxybenzophenone
42.80 g water
51.25 g ethanol
100.00 g
4.3 pH
______________________________________
Example 21: Hair Care Fixing Lotion
______________________________________
0.75 g 64-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.60 : propylamine
4.00 g vinylpyrrolidone/vinyl acetate copolymer
1.20 g DL-2-pyrrolidone-5-carboxylic acid
0.40 g hydrogenated rhizonic oil, ethoxylated with
40 Mol ethyleneoxide
0.20 g perfume
93.45 g water
100.00 g
3.8 pH value
______________________________________
Example 22: Foam Fixing Composition for Strong Fixing
______________________________________
0.30 g 64-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.60 : propylamine
5.00 g vinylpyrrolidone/vinyl acetate copolymer
0.60 g DL-2-pyrrolidone-5-carboxylic acid
0.45 g glyceryl laurate
0.15 g perfume
0.06 g cetyltrimethylammonium chloride
5.00 g propane/butane (5.0 bar)
10.00 g ethanol
78.44 g water
100.00 g
3.8 pH value
______________________________________
Example 23: Foam Fixing Composition
______________________________________
0.60 g 8-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.4 : propylamine
1.80 g chitosan
1.10 g formic acid
0.20 g 1,2-propylene glycol
0.20 g perfume
0.10 g cetyltrimethylammonium chloride
6.00 g propane/butane (5.0 bar)
10.00 g ethanol
80.00 g water
100.00 g
4.1 pH value
______________________________________
Example 24: Foam Fixing Composition
______________________________________
0.70 g 16-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.12 : propylamine
3.15 g polyvinylpyrrolidone
1.60 g citric acid
0.60 g hydrogenated rhizonic oil, ethoxylated with
45 Mol ethylene oxide
0.22 g decylpolyglucoside
0.20 g vinylpyrrolidone/methacrylamidopropyl-
trimethylammonium chloride copolymer
0.20 g perfume
6.00 g propane/butane (5.0 g)
87.33 g water
100.00 g
3.7 pH value
______________________________________
Example 25: Porous Foam Fixing Composition
______________________________________
0.50 g 4-cascade: 1,4-diaminobutane[4]:
propylamine
2.20 g vinylimidazolium methochloride/1-vinyl-
2-pyrrolidone copolymer
1.00 g glucose syrup
0.70 g oleylpolyethylene glycol-(200)-ether
0.60 g citric acid
0.10 g perfume
7.00 g propane/butane (5.0 bar)
10.00 g ethanol
77.90 g water
100.00 g
6.3 pH value
______________________________________
Example 26: Care-providing Foam Fixing Composition
______________________________________
0.8 g 32-cascade: 1,4-diaminobutane[4].:
(1-aza-butylidene).sup.28 : propylamine
6.0 g vinylcaprolactam/vinylpyrrolidone/dimethyl-
aminoethylmetacrylate terpolymer
0.6 g formic acid
0.2 g cetyltrimethylammonium chloride
0.2 g hydrogenated rhizonic oil, ethoxylated with
45 Mol ethylene oxide
0.2 g perfume
92.0 g water
100.00 g
4.4 pH value
______________________________________
The above composition is filled in a ratio of 94:6 with a propane-butane-propellant gas mixture.
Example 27: Dyeing and Fixing Composition
______________________________________
0.23 g 8-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.4 : propylamine
2.50 g vinyl acetate/crotonic acid/polyglycol
copolymer
0.20 g perfume
0.07 g 1-amino-4-(2',3'-dehydroxypropyl) amino-
5-chloro-2-nitrobenzene
0.05 g Basic Brown 17(C.I. 12 251)
0.01 g Basic Blue 7(C.I. 42 595)
0.0023 g Basic Violet 14 (C.I. 42 510)
46.94 g water
50.00 g ethanol
100.00 g
8.1 pH value
______________________________________
Example 28: Hair Spray with Strong Fixing Effect
______________________________________
0.30 g 4-cascade: 1,4-diaminobutane[4]:
propylamine
5.00 g t-octylacrylamide/acrylic acid/t-butyl-
aminoethylmethacrylate terpolymer
0.58 g 2-amino-2-methyl-1-propanol
0.15 g perfume
40.00 g 1,1-difluroethane
53.97 g ethanol
100.0 g
9.0 pH value (diluted with water 1:1)
______________________________________
Example 29: Hair Spray
______________________________________
0.55 g 4-cascade: 1,4-diaminobutane[4]:
propylamine
3.50 g vinyl acetate/crotonic acid/polyglycol
copolymer
0.15 g perfume
0.14 g formic acid
45.00 g 1,1-difluroethane
50.66 g ethanol
100.0 g
8.1 pH value (diluted with water 1:1)
______________________________________
Example 30: Hair Styling Spray
______________________________________
0.40 g 32-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.28 : propylamine
6.50 g vinyl pyrrolidone/vinyl acetate
copolymer
0.17 g formic acid
0.10 g perfume
10.67 g butane(1.5 bar)
33.33 g 1,1-difluroethane
42.83 g ethanol
100.0 g
7.1 pH value (diluted with water 1:1)
______________________________________
Example 31: 80% VOC Hair spray
______________________________________
0.20 g 4-cascade: 1,4-diaminobutane[4]:
propylamine
4.00 g t-butylacrylate/ethylacrylate/methacrylic
acid terpolymer
0.72 g 2-amino-2-methyl-1-propanol
0.20 g cyclo-tetra(dimethylsiloxane)
0.05 g perfume
15.00 g water
39.83 g ethanol
40.00 g dimethylether
100.0 g
9.1 pH value (diluted with water 1:1)
______________________________________
Example 32: Pump Hair Spray
______________________________________
0.27 g 4-cascade: 1,4-diaminobutane[4]:
propylamine
4.50 g t-octylacrylamide/acrylic acid/t-butyl-
aminoethylmethacrylate terpolymer
0.52 g 2-amino-2-methyl-1-propanol
0.30 g perfume
0.10 g dimethylsiloxane/ethylene glycol copolymer
6.31 g water
88.00 g ethanol
100.0 g
8.9 pH value (diluted with water 1:1)
______________________________________
Example 33: 80% VOC Pump Hair Spray
______________________________________
0.60 g 64-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.60 :propylamine
5.00 g vinyl pyrrolidone/vinyl acetate
copolymer
0.30 g perfume
0.26 g formic acid
13.84 g water
80.00 g ethanol
100.0 g
5.7 pH value (diluted with water 1:1)
______________________________________
Example 34: 55% VOC Pump Hair Spray
______________________________________
0.79 g 8-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.4 : propylamine
3.50 g vinyl acetate/crotonic acid
copolymer
0.20 g perfume
0.28 g formic acid
40.23 g water
55.00 g ethanol
100.0 g
7.7 pH value
______________________________________
Example 35: Hair Gel
______________________________________
0.60 g 16-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.12 : propylamine
2.50 g hydroxypropylmethyl cellulose
0.80 g polyoxyethylene-(20)-sorbitan monopalmitate
0.50 g polyoxyethylene-(25)-p-aminobenzoic acid
0.40 g formic acid
0.12 g cis-1-(3-chlorallyl)-3,5,7-triaza-1-
azoniadamatane chloride
0.10 g perfume
23.00 g glycerol
71.98 g water
100.00 g
5.4 pH value
______________________________________
Example 36: Hair Styling Fixing Gel
______________________________________
0.40 g 32-cascade: 1,4-diaminobutane[4]:
(1-aza-butylidene).sup.28 : propylamine
2.50 g polyvinyl pyrrolidone
2.00 g hydroxypropyl guar
0.80 g hydrogenated rhizonic oil, ethoxylated with
45 Mol of ethylene oxide
0.60 g DL-2-pyrrolidone-5-carboxylic acid
0.45 g sodium benzoate
0.30 g hydroxyethylcellulose
0.20 g perfume
0.09 g sodium formate
0.05 g mica/titanium oxide/zinc oxide powder
(Soloron ® Silver Sparkle of Merck, Germany)
92.61 g water
100.00 g
6.6 pH value
______________________________________
Example 37: Hair Fixing Liquid-Gel
______________________________________
1.00 g 4-cascade: 1,4-diamino-
butane[4]: propylamine
3.00 g vinyl pyrrolidone/vinyl acetate
copolymer
1.80 g polyoxyethylene-(20)-sorbitan monopalmitate
1.35 g polyethylene glycol-(45)
1.05 g hydroxyethyl cellulose
1.00 g citric acid
0.20 g 1,2-dibromo-2,4-dicyanobutane
0.20 g perfume
30.40 g water
100.00 g
7.5 pH value
______________________________________
Unless otherwise indicated, all percentages are percentages by weight.
Example 38: Comparative Measurements of Wet and Dry Combability
The wet combability and dry combability of hair treated with four aqueous solutions A to D according to the present invention were measured and compared with the measured wet and dry combability of hair treated with five aqueous solution containing standard hair care polymers.
Standard hair samples of the same length, each 17 cm long and 2.5 cm width, were first bleached with bleaching powder and 9 percent hydrogen peroxide solution for 30 minutes, then rinsed for two minutes, washed twice with a standard cleansing agent, rinsed again and brought to a uniform weight after drying.
After preliminary combing and adjustment to a residual moisture of 50%, 0.5 ml of each polymer solution is applied to one of the individual samples uniformly and placed in a foil pocket. After an acting time of 5 minutes, the combing forces for both wet combing and also dry combing were measured after drying the wet combed strand after the wet combing.
Table I shows the principle polymer ingredient of each tested solution and its concentration in the solution as well as the pH of the solution. Table II below shows the wet combing force and the dry combing force of each sample. The average combing force of an untreated control sample of hair amounted to 0.47N. The compositions A to D according to the invention have clearly reduced combing force results in comparison to those of the prior art.
TABLE I
______________________________________
Composition and Properties of Tested Solutions
Sample
Polymer Concentration
pH
______________________________________
A 4-cascade: 1,4-diamino-
1.50% 6.0
butane[4]:propylamine
B 4-cascade: 1,4-diamino-
0.25% 3.5
butane [4]: propylamine
C 64-cascade: 1,4-diaminobutane[4]:
0.25% 6.0
(1-aza-butylidene).sup.60 : propylamine
D 64-cascade: 1,4-diaminobutane[4]:
1.50% 3.5
(1-aza-butylidene).sup.60 : propylamine
E Vinylpyrrolidone/dimethylamino-
0.25% 6.0
ethylmethacrylate copolymer
F Vinylpyrrolidone/dimethylamino-
1.50% 3.5
ethylmethacrylate copolymer
G Vinylpyrrolidone/dimethylamino-
0.25% 3.5
ethylmethacrylate copolymer
H cationic hydroxypropyl cellulose
1.50% 6.0
I cationic hydroxypropyl cellulose
0.25% 3.5
______________________________________
TABLE II
______________________________________
Measured Wet and Dry Combing Force for
Compositions according to the Invention and Prior Art
Sample Wet combing Force,N
Dry combing Force,N
______________________________________
A 0.279 0.141
B 0.261 0.122
C 0.284 0.251
D 0.257 0.217
E 0.371 0.261
F 0.313 0.399
G 0.387 0.235
H 0.390 0.252
I 0.407 0.254
______________________________________
The disclosure in German Patent Application 196 25 928.7 of Jun. 28, 1996 is incorporated here by reference. This German Patent Application describes the invention described hereinabove and claimed in the claims appended herein in below and provides the basis for a claim of priority for the instant invention under 35 U.S.C. 119.
While the invention has been illustrated and described as embodied in a cosmetic composition for hair treatment with dendrimers, it is not intended to be limited to the details shown, since various modifications and changes may be made without departing in any way from the spirit of the present invention.
Without further analysis, the foregoing will so fully reveal the gist of the present invention that others can, by applying current knowledge, readily adapt it for various applications without omitting features that, from the standpoint of prior art, fairly constitute essential characteristics of the generic or specific aspects of this invention.
What is claimed is new and is set forth in the following appended claims.
Claims (4)
1. A method of treating hair comprising the steps of:
a) applying from 5 to 30 grams of a hair treatment composition to hand-towel-dried hair, according to the hair abundance,
b) allowing the hair treatment composition to remain on the hair for from 3 to 15 minutes, and
c) after step b), rinsing the hair treatment composition out of the hair and drying the hair;
wherein the hair treatment composition contains 0.01 to 75 percent by weight of at least one dendrimer and at least one cosmetic ingredient for hair treatment, in a cosmetic foundation or base; wherein said at least one cosmetic ingredient for hair treatment is at least one keratin-reducing mercapto compound for permanent hair shaping, at least one oxidizing agent for an oxidative after-treatment in said permanent hair shaping, at least one hair fixing polymer, at least one hair bleaching agent, at least one direct-dyeing hair dye compound, or a combination of at least one coupler substance and at least one developer substance for oxidative hair dyeing.
2. A method of treating hair comprising the steps of:
a) applying from 5 to 30 grams of a hair treatment composition to hand-towel-dried hair, according to the hair abundance, and
b) allowing the hair treatment composition to remain on the hair;
wherein the hair treatment composition contains 0.01 to 75 percent by weight of at least one dendrimer and at least one cosmetic ingredient selected from the group consisting of hair care-giving materials and hair fixing compounds.
3. A method of cleansing hair comprising the steps of:
a) applying from 5 to 30 grams of a hair cleansing composition to hand-towel-dried hair, according to the hair abundance,
b) allowing the hair cleansing composition to remain on the hair for from 3 to 15 minutes, and
c) after step b), rinsing the hair treatment composition out of the hair and drying the hair; and
wherein the hair cleansing composition contains 50 to 90 percent by weight water, 0.01 to 25 percent by weight of at least one anionic, cationic, amphoteric or non-ionic surfactant, and 0.1 to 35 percent by weight of at least one dendrimer, in a cosmetic base or foundation, and
wherein said at least one dendrimer is a poly(iminopropane-1,3-diyl)-dendrimer with nitrile and/or amino end groups.
4. A method of treating hair comprising the steps of:
a) applying from 5 to 30 grams of a hair treatment composition to hand-towel-dried hair, according to the hair abundance,
b) allowing the hair treatment composition to act on the hair for from 3 to 15 minutes, and
c) rinsing the hair treatment composition from the hair;
wherein the hair treatment composition contains 0.01 to 75 percent by weight of at least one dendrimer and at least one cosmetic ingredient selected from the group consisting of hair care-giving materials and hair fixing compounds.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19625928 | 1996-06-28 | ||
| DE19625982A DE19625982A1 (en) | 1996-06-28 | 1996-06-28 | Cosmetic agent for hair treatment with dendrimers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US6068835A true US6068835A (en) | 2000-05-30 |
Family
ID=7798319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US08/883,924 Expired - Lifetime US6068835A (en) | 1996-06-28 | 1997-06-27 | Cosmetic compositions for hair treatment containing dendrimers or dendrimer conjugates |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6068835A (en) |
| EP (1) | EP0815827B1 (en) |
| JP (1) | JPH1045545A (en) |
| AR (1) | AR007376A1 (en) |
| BR (1) | BR9703795A (en) |
| DE (2) | DE19625982A1 (en) |
| ES (1) | ES2114842T3 (en) |
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|---|---|---|---|---|
| US6432423B1 (en) * | 1997-12-19 | 2002-08-13 | L'oreal | Use of hyperbranched polymers and dendrimers comprising a particular group as film-forming agent, film-forming compositions comprising same and use particularly in cosmetics and pharmaceutics |
| US6475495B1 (en) * | 1997-12-19 | 2002-11-05 | L'oreal, S.A. | Hyperbranched polymers or dendrimers containing a particular group, preparation process, use and compositions comprising them |
| US20030114342A1 (en) * | 2001-09-20 | 2003-06-19 | Lonza Inc. | Compositions comprising quaternary ammonium compounds and dendritic polymers with antimicrobial activity |
| US6582685B1 (en) * | 1999-09-02 | 2003-06-24 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Hydroxyl-functionalized dendritic macromolecules in topical cosmetic and personal care compositions |
| US20030172472A1 (en) * | 2000-06-30 | 2003-09-18 | Florence Laurent | Oxidaton dyeing composition for keratinous fibres comprising an amphoteric polymer with fatty chain |
| US20040019981A1 (en) * | 2000-11-08 | 2004-02-05 | Francois Cottard | Direct dyeing composition for keratinous fibres comprising a cationic associative polyurethane |
| US20040025266A1 (en) * | 2000-11-08 | 2004-02-12 | Francois Cottard | Oxidation dyeing composition for karatinous fibres comprising a cationic associative polyurethane |
| US20040034947A1 (en) * | 2000-11-08 | 2004-02-26 | Frederic Legrand | Bleachng composition for keratinous fibres comprising an associate polyurethane |
| US20040034946A1 (en) * | 2000-11-08 | 2004-02-26 | Frederic Legrand | Composition for bleaching or permanent waving of keratinous fibers comprising a cationic associative polyurethane |
| US20040127581A1 (en) * | 2002-12-31 | 2004-07-01 | Baran Jimmie R. | Stabilized foams including surface-modified organic molecules |
| US20040127612A1 (en) * | 2002-12-31 | 2004-07-01 | Baran, Jimmie R. | Emulsions including surface-modified organic molecules |
| US6794346B2 (en) * | 2001-10-26 | 2004-09-21 | S.C. Johnson & Son, Inc. | Hard surface cleaners containing chitosan and furanone |
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| WO2005032498A3 (en) * | 2003-09-29 | 2005-07-21 | Rhodia Chimie Sa | Aqueous composition comprising a polyionic dendritic polymer and an ionic surface active agent |
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| WO2005092275A1 (en) * | 2004-03-26 | 2005-10-06 | L'oreal | Cosmetic composition comprising a dendritic polymer with peripheral fatty chains, a surfactant and a cosmetic agent, and uses thereof |
| US20050233943A1 (en) * | 1999-04-30 | 2005-10-20 | Benjamin Frydman | Novel polyamine analog conjugates and quinone conjugates as therapies for cancers and prostate diseases |
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| US20080038215A1 (en) * | 2004-08-17 | 2008-02-14 | Leo Derici | Hair Care Composition Comprising a Dendritic Macromolecule |
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| US20190008147A1 (en) * | 2015-08-24 | 2019-01-10 | Lanxess Deutschland Gmbh | Composition containing 1,2-dibromo-2,4-dicyanobutane (dbdcb) and at least one organic acid and/or the derivatives thereof |
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| DE102005063096A1 (en) * | 2005-12-30 | 2007-07-05 | Henkel Kgaa | Cosmetic agent, useful for protecting skin and hair before resoiling, cleaning skin and hair and restructuring the keratin fibers, preferably in human hair, comprises an hyperbranched polyester and/or polyester amide |
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Cited By (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6475495B1 (en) * | 1997-12-19 | 2002-11-05 | L'oreal, S.A. | Hyperbranched polymers or dendrimers containing a particular group, preparation process, use and compositions comprising them |
| US6432423B1 (en) * | 1997-12-19 | 2002-08-13 | L'oreal | Use of hyperbranched polymers and dendrimers comprising a particular group as film-forming agent, film-forming compositions comprising same and use particularly in cosmetics and pharmaceutics |
| US20050233943A1 (en) * | 1999-04-30 | 2005-10-20 | Benjamin Frydman | Novel polyamine analog conjugates and quinone conjugates as therapies for cancers and prostate diseases |
| US20080194697A1 (en) * | 1999-04-30 | 2008-08-14 | Benjamin Frydman | Novel polyamine analog conjugates and quinone conjugates as therapies for cancers and prostate diseases |
| US7279502B2 (en) | 1999-04-30 | 2007-10-09 | Cellgate, Inc. | Polyamine analog conjugates and quinone conjugates as therapies for cancers and prostate diseases |
| US6582685B1 (en) * | 1999-09-02 | 2003-06-24 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Hydroxyl-functionalized dendritic macromolecules in topical cosmetic and personal care compositions |
| US20030172472A1 (en) * | 2000-06-30 | 2003-09-18 | Florence Laurent | Oxidaton dyeing composition for keratinous fibres comprising an amphoteric polymer with fatty chain |
| US7066965B2 (en) * | 2000-11-08 | 2006-06-27 | L'oreal S.A. | Bleaching composition for keratinous fibers comprising an associate polyurethane |
| US20040034947A1 (en) * | 2000-11-08 | 2004-02-26 | Frederic Legrand | Bleachng composition for keratinous fibres comprising an associate polyurethane |
| US7077869B2 (en) * | 2000-11-08 | 2006-07-18 | L'oreal S.A. | Composition for bleaching or permanent waving of keratinous fibers comprising a cationic associative polyurethane |
| US7101405B2 (en) * | 2000-11-08 | 2006-09-05 | L'oreal S.A. | Oxidation dyeing composition for karatinous fibers comprising a cationic associative polyurethane |
| US20040025266A1 (en) * | 2000-11-08 | 2004-02-12 | Francois Cottard | Oxidation dyeing composition for karatinous fibres comprising a cationic associative polyurethane |
| US7108726B2 (en) * | 2000-11-08 | 2006-09-19 | L'oreal S.A. | Direct dyeing composition for keratinous fibres comprising a cationic associative polyurethane |
| US20040034946A1 (en) * | 2000-11-08 | 2004-02-26 | Frederic Legrand | Composition for bleaching or permanent waving of keratinous fibers comprising a cationic associative polyurethane |
| US20040019981A1 (en) * | 2000-11-08 | 2004-02-05 | Francois Cottard | Direct dyeing composition for keratinous fibres comprising a cationic associative polyurethane |
| US20030114342A1 (en) * | 2001-09-20 | 2003-06-19 | Lonza Inc. | Compositions comprising quaternary ammonium compounds and dendritic polymers with antimicrobial activity |
| US20050080144A1 (en) * | 2001-10-16 | 2005-04-14 | Benjamin Frydman | Oligoamine compounds and derivatives thereof for cancer therapy |
| US7491849B2 (en) | 2001-10-16 | 2009-02-17 | Progen Pharmaceuticals, Inc. | Oligoamine compounds and derivatives thereof for cancer therapy |
| US6849586B2 (en) * | 2001-10-26 | 2005-02-01 | S. C. Johnson & Son, Inc. | Hard surface cleaners containing chitosan |
| US6794346B2 (en) * | 2001-10-26 | 2004-09-21 | S.C. Johnson & Son, Inc. | Hard surface cleaners containing chitosan and furanone |
| US20050271615A1 (en) * | 2002-08-30 | 2005-12-08 | Doron Shabat | Self-immolative dendrimers releasing many active moieties upon a single activating event |
| US7129277B2 (en) | 2002-12-31 | 2006-10-31 | 3M Innovative Properties Company | Emulsions including surface-modified inorganic nanoparticles |
| US7001580B2 (en) | 2002-12-31 | 2006-02-21 | 3M Innovative Properties Company | Emulsions including surface-modified organic molecules |
| US20060002843A1 (en) * | 2002-12-31 | 2006-01-05 | 3M Innovative Properties Company | Emulsions including surface-modified organic molecules |
| US20040127581A1 (en) * | 2002-12-31 | 2004-07-01 | Baran Jimmie R. | Stabilized foams including surface-modified organic molecules |
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| CN116751260A (en) * | 2023-04-11 | 2023-09-15 | 苏州有诺真生物科技有限公司 | A method for generating size-controllable universal polymeric chromophores through cascade polymerization |
| CN116751260B (en) * | 2023-04-11 | 2024-05-28 | 苏州有诺真生物科技有限公司 | A method for generating a universal multi-colorant with controllable size by cascade polymerization |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0815827A2 (en) | 1998-01-07 |
| AR007376A1 (en) | 1999-10-27 |
| EP0815827B1 (en) | 2003-07-30 |
| EP0815827A3 (en) | 1999-11-10 |
| ES2114842T3 (en) | 2004-04-16 |
| BR9703795A (en) | 1998-09-01 |
| DE19625982A1 (en) | 1998-01-02 |
| DE59710494D1 (en) | 2003-09-04 |
| ES2114842T1 (en) | 1998-06-16 |
| JPH1045545A (en) | 1998-02-17 |
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